Imatinib mesylate, 4-(4-methylpiperazin-1-ylmethyl)-N-[4-methyl-3-[(4-pyrinin-3-yl)pyrimidin-2-ylamino]phenyl]benzamide mesylate, is a compound having the chemical structure

Imatinib is a protein-tyrosine kinase inhibitor. It is especially useful in the treatment of various types of cancer, and can also be used for the treatment of atherosclerosis, thrombosis, restenosis, and fibrosis. Thus imatinib can also be used for the treatment of non-maligant diseases. Imatinib is usually administered orally in the form of a suitable salt, e.g., in the form of imatinib mesylate.
Patent Application Publication Nos. WO 99/03854, WO 2005/077933, WO 2005/095379, WO 2004/106326, WO 2006/054314, WO 2006/024863, WO 2006/048890, US2006/0030568, and WO 2007/023182 and U.S. Pat. No. 6,894,051 purportedly describe amorphous imatinib and crystalline forms of imatinib mesylate designated forms H1, α, α2, β, δ, ε, I, and II.
WO 99/03854, US2006/0030568, and U.S. Pat. No. 6,894,051 purportedly disclose imatinib mesylate forms α and β. Form α is characterized therein by powder X-ray diffraction (“PXRD”) pattern having peaks at 4.9, 10.5, 14.9, 16.5, 17.7, 18.1, 18.6, 19.1, 21.3, 21.6, 22.7, 23.2, 23.8, 24.9, 27.4, 28.0, and 28.6±0.2 °2θ. Form β is characterized therein by PXRD pattern having peaks at 9.7, 13.9, 14.7, 17.5, 18.2, 20.0, 20.6, 21.1, 22.1, 22.7,23.8, 29.8, and 30.8±0.2 °2θ.
WO 2005/077933 purportedly discloses imatinib mesylate crystalline form α2, which is defined herein by a PXRD pattern having peaks at 4.8, 10.4, 11.2, 11.9, 12.9, 13.8, 14.9, 16.4, 17.0, 17.6, 18.1, 18.6, 19.0, 19.8, 21.2, 21.6, 22.6, 23.1, 23.7, 24.9, 26.3, 27.3, 28.5, 31.9, 32.5, and 43.4±0.2 °2θ.
WO 2004/106326 purportedly discloses imatinib mesylate crystalline form H1, which is defined herein by PXRD pattern having peaks at 9.9, 11.1, 16.3, 17.3, 18.1, 19.1, 19.6, 20.3, 21.1, 21.9, 23.2, 23.6, 24.2, 24.9, 25.6, 26.0, 27.3, 27.9, 28.9, 29.4, 30.4, and 30.5±0.2 °2θ. WO 2004/106326 also purportedly discloses amorphous imatinib mesylate hydrate having water content of 2.0-3.2%.
WO 2006/054314 purportedly discloses imatinib mesylate crystalline forms I and II, which are defined herein by PXRD pattern having peaks at 9.7, 10.0, 10.8, 12.5, 13.0, 14.0, 15.2, 16.0, 17.1, 17.9, 18.9, 19.3, 20.0, 20.9, 21.7, 22.4, 23.0, 24.7, 25.2, 25.8, 27.1, 28.0, 28.7, 29.2, 30.2, 30.9, 31.4, 33.3, 36.4, and 38.3±0.2 °2θ, and by peaks at 2.4, 2.8, 4.4, 4.9, 5.5, 7.9, 8.4, 8.9, 9.6, 11.1, 11.5, 12.1, 12.7, 14.1, 14.7, 15.3, 16.1, 17.0, 17.6, 18.6, 19.4, 19.6, 20.3, 20.7, 21.4, 22.0, 22.7, 23.5, 24.0, 24.6, 25.2, 25.7, 26.9, 27.7, 28.2, 28.6, 29.1, 28.5, 30.130.6, 21.8, 33.5, 34.4, 34.9, 35.7, 35.9, 37.1, 37.5, 37.9, 37.2, 39.7, 40.6, 41.3, 43.4, 43.8, 44.6, 45.2, 45.7, 46.5, 47.1, and 48.0±0.2 °2θ, respectively.
WO 2007/023182 purportedly discloses imatinib mesylate crystal forms δ and ε. Form δ is defined herein by PXRD pattern having peaks at 19.2, 19.4, 19.8, 20.3, 20.7, 20.9, and 21.1±0.2 °2θ, and form ε is defined herein by PXRD pattern having peaks at 13.9, 17.0, 17.9, 18.5, 19.6, 20.7, and 24.1±0.2 °2θ. International Patent Application No. WO 2007/136510 describes additional crystalline forms of imatinib mesylate including forms V and X which are described in further detail below.
WO 2003/090720 relates to tablet containing about 30-80% w/w imatinib. Further, WO 01/47507 describes a pharmaceutical composition/tablet containing about 22% w/w imatinib mesylate. Both US 2006/0275372 and WO 2007/119601 describe nanoparticulate compositions of imatinib mesylate.